The complexity of urban contexts is often subsumed into generalizations and deficit assumptions of urban communities and its members by those unfamiliar with urban culture. This is especially true for teachers seeking work in urban schools. This article addresses the complex interpretations of urban through the lens of a White male graduate student teacher, Nathan, as he contemplates his experiences in urban school settings. The trajectory of his understanding of the complex nature of urban realities that influence the work of urban teachers and the lives of their students is discussed. The article concludes with implications for urban teacher education programs and teacher educators.